JP4346823B2 - エタンから酢酸への酸化用触媒 - Google Patents
エタンから酢酸への酸化用触媒 Download PDFInfo
- Publication number
- JP4346823B2 JP4346823B2 JP2000590777A JP2000590777A JP4346823B2 JP 4346823 B2 JP4346823 B2 JP 4346823B2 JP 2000590777 A JP2000590777 A JP 2000590777A JP 2000590777 A JP2000590777 A JP 2000590777A JP 4346823 B2 JP4346823 B2 JP 4346823B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- ethane
- acetic acid
- mixture
- oxidation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 117
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 19
- 230000003647 oxidation Effects 0.000 title claims abstract description 18
- 239000003054 catalyst Substances 0.000 title claims description 81
- 239000007789 gas Substances 0.000 claims abstract description 11
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 9
- 229910052733 gallium Inorganic materials 0.000 claims abstract description 8
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 6
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 14
- 239000005977 Ethylene Substances 0.000 claims description 14
- 229910052720 vanadium Inorganic materials 0.000 claims description 10
- 229910052758 niobium Inorganic materials 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- QIJNJJZPYXGIQM-UHFFFAOYSA-N 1lambda4,2lambda4-dimolybdacyclopropa-1,2,3-triene Chemical compound [Mo]=C=[Mo] QIJNJJZPYXGIQM-UHFFFAOYSA-N 0.000 claims 1
- 229910039444 MoC Inorganic materials 0.000 claims 1
- 238000001354 calcination Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229910001868 water Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910052750 molybdenum Inorganic materials 0.000 description 9
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 8
- 239000011733 molybdenum Substances 0.000 description 8
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000010955 niobium Substances 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- -1 unsaturated aliphatic aldehydes Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 229910052721 tungsten Inorganic materials 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052746 lanthanum Inorganic materials 0.000 description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 2
- 150000002940 palladium Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- FIXLYHHVMHXSCP-UHFFFAOYSA-H azane;dihydroxy(dioxo)molybdenum;trioxomolybdenum;tetrahydrate Chemical compound N.N.N.N.N.N.O.O.O.O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O FIXLYHHVMHXSCP-UHFFFAOYSA-H 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 239000012229 microporous material Substances 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 239000007783 nanoporous material Substances 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/652—Chromium, molybdenum or tungsten
- B01J23/6525—Molybdenum
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/219,702 US6060421A (en) | 1998-12-23 | 1998-12-23 | Catalysts for the oxidation of ethane to acetic acid, methods of making and using the same |
US09/219,702 | 1998-12-23 | ||
PCT/EP1999/010186 WO2000038833A1 (en) | 1998-12-23 | 1999-12-15 | Catalyst for the oxidation of ethane to acetic acid |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2002537085A JP2002537085A (ja) | 2002-11-05 |
JP4346823B2 true JP4346823B2 (ja) | 2009-10-21 |
Family
ID=22820416
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000590777A Expired - Fee Related JP4346823B2 (ja) | 1998-12-23 | 1999-12-15 | エタンから酢酸への酸化用触媒 |
Country Status (8)
Country | Link |
---|---|
US (2) | US6060421A (es) |
EP (1) | EP1058579B1 (es) |
JP (1) | JP4346823B2 (es) |
AT (1) | ATE336297T1 (es) |
DE (1) | DE69932806T2 (es) |
ES (1) | ES2270629T3 (es) |
TW (1) | TW476665B (es) |
WO (1) | WO2000038833A1 (es) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6087297A (en) * | 1998-06-29 | 2000-07-11 | Saudi Basic Industries Corporation | Catalysts for gas phase production of acetic acid from ethane, processes of making the same and methods of using same |
US6143921A (en) | 1999-05-14 | 2000-11-07 | Saudi Basic Industries Corporation | Method for producing vinyl acetate monomer from ethane or ethylene oxidation |
US6258992B1 (en) * | 1999-09-17 | 2001-07-10 | Saudi Basic Industries Corporation | Gas phase catalytic oxidation of hydrocarbons to carboxylic acids and dehydrogenated products |
US6693059B2 (en) * | 2000-02-09 | 2004-02-17 | Rohm And Haas Company | Process for preparing a catalyst and catalytic oxidation therewith |
US6337424B1 (en) * | 2000-04-28 | 2002-01-08 | Saudi Basic Industries Corporation | Catalysts oxidation of lower olefins to unsaturated aldehydes, methods of making and using the same |
US6444845B1 (en) * | 2000-04-28 | 2002-09-03 | Saudia Basic Industries Corporation | Process for the oxidation of unsaturated aldehydes to produce carboxylic acids using Mo-V based catalysts |
US6531631B1 (en) | 2000-04-28 | 2003-03-11 | Saudi Basic Industries Corporation | Oxidation of ethane to acetic acid and ethylene using molybdenum and vanadium based catalysts |
US7038082B2 (en) | 2002-10-17 | 2006-05-02 | Basf Aktiengesellschaft | Preparation of a multimetal oxide material |
UA79540C2 (uk) * | 2003-01-27 | 2007-06-25 | Бп Кемікалз Лімітед | Каталітична композиція окиснення, її одержання та спосіб селективного окиснення |
WO2007001649A2 (en) * | 2005-06-22 | 2007-01-04 | Exxonmobil Chemical Patents Inc. | Oxidation of alkanes |
DE102010001399A1 (de) | 2010-01-29 | 2011-08-04 | Wacker Chemie AG, 81737 | Verfahren zur Herstellung von Carbonsäuren mit 1-3 Kohlenstoff-atomen aus nachwachsenden Rohstoffen |
CN107029700B (zh) * | 2017-05-08 | 2019-11-26 | 厦门大学 | 一种丙烷氨氧化制丙烯腈的催化剂及其制备方法 |
WO2020194228A1 (en) | 2019-03-26 | 2020-10-01 | Sabic Global Technologies B.V. | Method of reactivating catalyst |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3131223A (en) * | 1957-01-04 | 1964-04-28 | Consortium Elektrochem Ind | Process for the production of aldehydes and ketones |
DE1129469B (de) * | 1957-09-28 | 1962-05-17 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden, Ketonen oder den Aldehyden entsprechenden Saeuren |
US3057915A (en) * | 1957-09-14 | 1962-10-09 | Hoechst Ag | Process for oxidizing olefins to aldehydes, ketones and acids |
US3240805A (en) * | 1961-10-13 | 1966-03-15 | Halcon International Inc | Process for producing acetic acid |
US4339355A (en) * | 1975-10-09 | 1982-07-13 | Union Carbide Corporation | Catalytic oxide of molybdenum, vanadium, niobium and optional 4th metal |
US4148757A (en) * | 1977-08-10 | 1979-04-10 | The Standard Oil Company | Process for forming multi-component oxide complex catalysts |
US4250346A (en) * | 1980-04-14 | 1981-02-10 | Union Carbide Corporation | Low temperature oxydehydrogenation of ethane to ethylene |
GB8915410D0 (en) * | 1989-07-05 | 1989-08-23 | Bp Chem Int Ltd | Chemical process |
US4524236A (en) * | 1984-06-28 | 1985-06-18 | Union Carbide Corporation | Process for oxydehydrogenation of ethane to ethylene |
US4568790A (en) * | 1984-06-28 | 1986-02-04 | Union Carbide Corporation | Process for oxydehydrogenation of ethane to ethylene |
US4596787A (en) * | 1985-04-11 | 1986-06-24 | Union Carbide Corporation | Process for preparing a supported catalyst for the oxydehydrogenation of ethane to ethylene |
US4899003A (en) * | 1985-07-11 | 1990-02-06 | Union Carbide Chemicals And Plastics Company Inc. | Process for oxydehydrogenation of ethane to ethylene |
US5162578A (en) * | 1987-06-12 | 1992-11-10 | Union Carbide Chemicals & Plastics Technology Corporation | Acetic acid from ethane, ethylene and oxygen |
JP3142549B2 (ja) * | 1990-09-10 | 2001-03-07 | 三菱レイヨン株式会社 | 鉄・アンチモン・モリブデン含有酸化物触媒組成物およびその製法 |
GB9022127D0 (en) * | 1990-10-11 | 1990-11-21 | Bp Chem Int Ltd | Process |
US5300682A (en) * | 1991-06-10 | 1994-04-05 | The Standard Oil Co. | Catalytic oxidation of ethane to acetic acid |
TW295579B (es) * | 1993-04-06 | 1997-01-11 | Showa Denko Kk | |
FR2705668B1 (fr) * | 1993-05-28 | 1995-08-25 | Rhone Poulenc Chimie | Procédé de préparation d'acide acétique par oxydation ménagée de l'éthane. |
DE19630832A1 (de) * | 1996-07-31 | 1998-02-05 | Hoechst Ag | Verfahren zur selektiven Herstellung von Essigsäure |
-
1998
- 1998-12-23 US US09/219,702 patent/US6060421A/en not_active Expired - Lifetime
-
1999
- 1999-12-15 WO PCT/EP1999/010186 patent/WO2000038833A1/en active IP Right Grant
- 1999-12-15 AT AT99964628T patent/ATE336297T1/de not_active IP Right Cessation
- 1999-12-15 EP EP99964628A patent/EP1058579B1/en not_active Expired - Lifetime
- 1999-12-15 ES ES99964628T patent/ES2270629T3/es not_active Expired - Lifetime
- 1999-12-15 DE DE69932806T patent/DE69932806T2/de not_active Expired - Lifetime
- 1999-12-15 JP JP2000590777A patent/JP4346823B2/ja not_active Expired - Fee Related
- 1999-12-22 TW TW088122637A patent/TW476665B/zh not_active IP Right Cessation
-
2000
- 2000-02-14 US US09/503,635 patent/US6130356A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JP2002537085A (ja) | 2002-11-05 |
US6060421A (en) | 2000-05-09 |
EP1058579A1 (en) | 2000-12-13 |
US6130356A (en) | 2000-10-10 |
DE69932806D1 (de) | 2006-09-28 |
ATE336297T1 (de) | 2006-09-15 |
EP1058579B1 (en) | 2006-08-16 |
WO2000038833A1 (en) | 2000-07-06 |
DE69932806T2 (de) | 2007-05-03 |
TW476665B (en) | 2002-02-21 |
ES2270629T3 (es) | 2007-04-01 |
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